1-(hex-5-ynyl)-3-phenylurea | 1402829-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(hex-5-ynyl)-3-phenylurea
• 英文别名: 1-Hex-5-ynyl-3-phenylurea；1-hex-5-ynyl-3-phenylurea
• CAS: 1402829-05-3
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: LZSDMMCWFWRGOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(hex-5-ynyl)-3-phenylurea 在 三乙胺 、 二溴三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到N-hex-5-yn-1-yl-N'-phenylcarbodiimide
  参考文献：
  名称：

  Determining the Regioregularity in Alkyne Polycarbodiimides and Their Orthogonal Modification of Side Chains To Yield Perfectly Alternating Functional Polymers

  摘要：

  To understand the structure-property relationship in functional macromolecules through side chain modulation, both the accurate determination of the position of modifiable groups along the polymer chain and their subsequent modifications using high fidelity methods are crucial. In this report, the polymer microstructure of a helical alkyne polycarbodiimide has directly been probed through N-15 NMR spectroscopy on isotopic labeled poly(N-(3-ethynylphenyl)-N-15'-hexyl)carbodiimide and found to be a highly regioregular polymer structure. This polymer undergoes facile and quantitative CuAAC "click" chemistry, yielding perfectly alternating functional polymers. Advances have been made through the synthesis of new optically active alkyne polycarbodiimides with two independently modifiable pendant groups per repeat unit of polymers. Orthogonal postmodifications of the pendant groups were then performed to incorporate two different sets of small molecules in the repeat unit of polymers in a controlled manner and under mild reaction conditions using either sequential CuAAC "click" reactions when two dissimilar alkyne groups are present or a combination of CuAAC and thiol-ene click chemistries when pendant groups bear alkyne and vinyl moieties.

  DOI：

  10.1021/ma301639m
• 作为产物：
  描述：

  5-己炔-1-胺 、 异氰酸苯酯 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到1-(hex-5-ynyl)-3-phenylurea
  参考文献：
  名称：

  Determining the Regioregularity in Alkyne Polycarbodiimides and Their Orthogonal Modification of Side Chains To Yield Perfectly Alternating Functional Polymers

  摘要：

  To understand the structure-property relationship in functional macromolecules through side chain modulation, both the accurate determination of the position of modifiable groups along the polymer chain and their subsequent modifications using high fidelity methods are crucial. In this report, the polymer microstructure of a helical alkyne polycarbodiimide has directly been probed through N-15 NMR spectroscopy on isotopic labeled poly(N-(3-ethynylphenyl)-N-15'-hexyl)carbodiimide and found to be a highly regioregular polymer structure. This polymer undergoes facile and quantitative CuAAC "click" chemistry, yielding perfectly alternating functional polymers. Advances have been made through the synthesis of new optically active alkyne polycarbodiimides with two independently modifiable pendant groups per repeat unit of polymers. Orthogonal postmodifications of the pendant groups were then performed to incorporate two different sets of small molecules in the repeat unit of polymers in a controlled manner and under mild reaction conditions using either sequential CuAAC "click" reactions when two dissimilar alkyne groups are present or a combination of CuAAC and thiol-ene click chemistries when pendant groups bear alkyne and vinyl moieties.

  DOI：

  10.1021/ma301639m

文献信息

• Determining the Regioregularity in Alkyne Polycarbodiimides and Their Orthogonal Modification of Side Chains To Yield Perfectly Alternating Functional Polymers
  作者：Januka Budhathoki-Uprety、James F. Reuther、Bruce M. Novak

  DOI：10.1021/ma301639m

  日期：2012.10.23

  To understand the structure-property relationship in functional macromolecules through side chain modulation, both the accurate determination of the position of modifiable groups along the polymer chain and their subsequent modifications using high fidelity methods are crucial. In this report, the polymer microstructure of a helical alkyne polycarbodiimide has directly been probed through N-15 NMR spectroscopy on isotopic labeled poly(N-(3-ethynylphenyl)-N-15'-hexyl)carbodiimide and found to be a highly regioregular polymer structure. This polymer undergoes facile and quantitative CuAAC "click" chemistry, yielding perfectly alternating functional polymers. Advances have been made through the synthesis of new optically active alkyne polycarbodiimides with two independently modifiable pendant groups per repeat unit of polymers. Orthogonal postmodifications of the pendant groups were then performed to incorporate two different sets of small molecules in the repeat unit of polymers in a controlled manner and under mild reaction conditions using either sequential CuAAC "click" reactions when two dissimilar alkyne groups are present or a combination of CuAAC and thiol-ene click chemistries when pendant groups bear alkyne and vinyl moieties.